


When in Rome...

by ficforthought



Series: Tumblr Ask Response Fics [7]
Category: Supernatural
Genre: Heavy Angst, M/M, Possibly Unrequited Love, Sexual Fantasy, Threats of Rape/Non-Con, Tortured Dean Winchester, Tumblr Ask Box Fic, Weecest, head fuck
Language: English
Status: Completed
Published: 2020-10-07
Updated: 2020-10-07
Packaged: 2021-03-07 16:07:35
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Underage
Chapters: 1
Words: 4,343
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26880388
Author URL: https://archiveofourown.org/users/ficforthought/pseuds/ficforthought
Summary: Written in response to the Tumblr Ask "In hell if Dean agrees to fuck a version of Sam he'll be taken off the rack for a day. What form of Sam would he choose?"This containsthreat of non-conhowever all explicit content is fully consensual. Tagged accordingly.
Relationships: Dean Winchester/Sam Winchester
Series: Tumblr Ask Response Fics [7]
Series URL: https://archiveofourown.org/series/1852207
Comments: 12
Kudos: 56





	When in Rome...

One minute Dean’s body is yet again sliced, carved and torn in ways he could never imagine, and the next he’s made whole by the power of whatever freaky magic Hell uses to heal people after a whole day of torture on the rack. Even now, just days shy of thirty years of this he breathes a sigh of relief at the all too temporary reprieve, knowing it won’t last more than the few minutes it takes for Alistair to make him the same offer he’s made every day since Dean’s arrival in the pit. It’s getting harder and harder to tell the demon to go and fuck himself, a sick feeling in his stomach every time, knowing this could well be the last time he has the strength to say no. He’s heard tales of people breaking after just a year, some lasted five and even fewer lasted ten so compared to that he’s been fighting far longer than anyone else, but everyone has their limits.  
  
The familiar sound of Alistair’s footsteps approaching makes him tense up, his heart beating faster as the demon stands alongside him and wipes blood off his giant knife with a rag. He has a bored looking expression on his face, as if putting the hunter through so much pain had lost its appeal, “Dean, Dean, Dean...” he says in that nasally whine of his, “what am I to do with you?” he starts to scrape dried blood from under his nails with the tip of the blade, “I think it’s time I made you a new offer.”  
  
Dean frowns, unable to stop himself fully lifting his head up in surprise at the unexpected change in events, “Whatever it is the answer’s still no, asshole,” he spits.  
  
A truly evil smirk crosses Alistair’s face as he bends down close to Dean’s, his putrid breath hot and moist against sweaty and bloody skin as he speaks, “Hmm, I think not. I’ve been inside your head,” he strokes the back of his hand almost tenderly down his victim’s cheek and Dean had to resist the urge to puke, “I _know_ what you want, Deano, I know _all_ of your depraved fantasies. And about your own brother, no less...”  
  
“You don’t know shit!” Dean shouts, heart racing even faster with panic. There’s very little he’s been able to keep to himself in his time here but he’s sure his feelings about Sammy have been so tightly caged that no-one would find out...well, sure until now, but demons lie all the time.  
  
“Come now, Dean, you can’t hide anything from me. All those memories of times you’ve wanted to do so many decidedly _non brotherly_ things to Sam, they’re…” he presses a long finger to Dean’s temple and taps in time with his words, “right...in...here.”  
  
“That’s bullshit,” the hunter replies, struggling against the hooks holding him down on the rack, knowing it’s futile but doing it anyway, “my job is to take care of Sammy and that’s what I’ve done.”  
  
“Mmm, that’s true,” the demon replies, taking a painful grip on Dean’s chin so he’s forced to keep eye contact with the black eyed bastard, “you’ve almost been a saint, you never touched him but ohhh, you’ve _wanted to_ for so, so long, haven’t you? I’ve seen countless thoughts about how you’ve watched him, imagining the filthy things you’d like to do to him if only you had the chance. All the times he’s come out of the bathroom in just a towel, you couldn't take your eyes off that gorgeous flesh, could you? You can’t tell me feeling his body against yours the night you went to get him from Stanford didn’t feel good, that’s why you pushed him off you when he pinned you to the floor, isn’t it? You _liked it_ but you didn’t want poor, beautiful, innocent Sammy to feel you getting hard for him, didn’t want him to know about your sick desires for him, did you, sweetheart? I can’t say I blame you, he’s a very handsome young man after all.”  
  
Mortification floods through Dean’s body at the words, he could deny it all he wants but if Alistair has been able to see that then he must have seen more, too, “Shut the fuck up!” he snaps, closing his eyes, trying to get the pictures and desires that have haunted him for years out of his head.  
  
“Ohhh, I don’t think so, my boy,” the demon singsongs, his voice full of glee, “what about that time not too long ago when Sammy made you promise to kill him. I can see it in your mind, Dean, him pleading with you, holding you, leaning in _so close_ , your face in his hands…it took everything you had not to kiss him, I can tell. But that’s not all you thought about, was it?”  
  
“I don’t know what you’re talking about,” Dean says through gritted teeth, grunting in pain as Alistair's grip tightens on his chin.  
  
“Now you’re just _lying_ , do I need to cut your tongue out just to teach you a lesson, Dean?”  
  
The hunter’s breaths come even faster, now, his eyes snapping open because the bastard has done that more than once so Dean couldn’t beg for the torture to stop, but the screams still echoed from his throat and Alistair fucking revelled in it. Of all the things Dean’s suffered, that's one of the things that hit him hardest, “No,” he rasps, shaking his head.  
  
“Tell me what you wanted to do to Sam that night...and don’t spare the details,” when Dean glares at him the only sign the demon has registered it is how his mouth is pinched slightly, “tell me and I’ll make you the new offer,” the tone is casual - _too_ casual - and the calmness is terrifying because the torture master always ups his game when Dean gets particularly defiant.  
  
Dean closes his eyes again, fighting the tears of shame that are burning behind the lids, “I wanted to touch him,” he croaks around the lump in his throat, “lying there, ass up in the air, looking all…” he pauses, his breath hitching with guilt.  
  
“Go on, darling,” Alistair coos, the glee evident in his voice, “looking all what?”  
  
The pet names the bastard insists on using makes Dean’s skin crawl, but he somehow pushes on, “vulnerable...pliant, and...”  
  
“Fuckable.” the demon finishes for him, “You wondered what it would be like to strip him, climb onto the bed and sink into that perfect ass, didn’t you?”  
  
A single tear escapes and runs down Dean’s face before he lets out a sob, nodding his head only slightly.  
  
Alistair gently thumbs away the tear, leaning in to whisper into his plaything’s ear, “Delicious, Dean, you have such potential.”  
  
“Fuck you!” Dean hisses, a fresh wave of disgust for both himself and the demon rolling through him.  
  
Alistair’s chuckle sounds so out of place that Dean blinks his eyes open and looks at him again, even though he’s worried about what expression he’ll see. He’s surprised when the look is almost fond, his eyes crinkling as he looks at Dean like he’s something precious, and it makes the hunter feel sick.  
  
“Very tempting offer,” he smirks, turning to run his eyes over Dean’s naked form before trailing his fingers from shoulder to ass, palming one of the firm cheeks. When Dean tenses the hell spawn ghosts a finger over his crack, keeping it there for a few seconds, no doubt to savour the fear before he pulls away and walks back to face the hunter, “but that’s a pleasure I’m saving for later. No, let me be clear...I want _you_ to fuck _Sam_ , Dean. Do that and I’ll take you off the rack for a day.”  
  
“What? No,” Dean barks out, disbelievingly, “you’re a sick fuck.”  
  
Alistair throws his head back and lets out a deep belly laugh which causes Dean to shiver in disgust. When the demon looks back at him he raises his arms, knife still clutched in one hand, “Look around you, darling, sickness and depravity is our lifeblood,” he leans in close again, “go on, you know you want to,” he says, like he’s trying to cajole Dean into an extra piece of pie instead of fucking his own brother, “pick a fantasy and I’ll make it happen. It won’t be real so you won’t be hurting your precious little Sammy, but it’ll _feel_ real, so real you won’t know the difference. You can be free to take exactly what you’ve wanted for so long. I can make him desperate and begging for your cock, or you can tie him up and use him as you see fit. He doesn’t even have to be a willing participant, in fact it’s so much more _fun_ that way. Nobody’s judging you, Dean...think of how good it would be to see your beloved brother, again. Don’t you want to know what it’s like to kiss him, to touch him, to _finally_ fuck that sweet little ass you’ve dreamed of for years, my dear? Wouldn’t that be so much better than feeling my little toys on your flesh?”  
  
To say Dean is conflicted would be the understatement of the fucking century. This is just another twisted way for Alistair to mess with his head even more. He wants the excruciating pain to stop, _of course_ he does, but can he really let the bastard get to him like this? He’s trying to push the thoughts of just seeing Sam away, it’s too painful, like someone’s crushing his heart in their fist, but on the other hand seeing even a fake version of his brother after nearly thirty years is ultimately too hard to resist. Defeated, he lets his body sag against the hooks, knowing that while he’s whole they don’t really hurt him, not compared to everything else, and he hears the smug laugh the demon lets out.  
  
“I need you to say it, Dean.”  
  
With guilt heavy in his stomach Dean lifts his head and glares at the creature. He's already in Hell, what's the worst that can happen? “ _Fine_ , take me off the rack and I’ll fuck Sammy.”  
  
Alistair puts his knife down on the trolley alongside the small selection of what Dean’s painfully aware is a vast collection of his instruments of torture and kneels down in front of him, lifting both hands to cup Dean’s face, “Good boy,” he says, “now what’s it to be?”  
  
The position Dean’s held in means he can’t turn away, though he angles his head away from the demon just on principle, “What?” he asks, confused.  
  
“The fantasy, what’s it to be?” he slides his hands up and presses his fingers to each of Dean’s temples, “Let me in and your wish is your command.”  
  
Another wave of nausea rolls in Dean’s stomach, both at the demon and at himself as he closes his eyes and allows a memory to fill his mind, one which over the years has morphed into one of his go to jerk off fantasies. He holds his breath and waits...and waits. He opens his eyes and looks at Alistair, terrified for a moment that _this_ was the torture, that he’s let the bastard see too much and he’ll forever use Dean’s shame against him, but what he sees is a look of mild surprise.  
  
“Well, well,” the demon says as a gleeful look spreads across his features, “isn’t that just _delicious_?” he wags a finger at Dean as his expression changes to one that’s almost pride, the nasally whine is back, “You definitely wouldn’t have gotten into Heaven with those thoughts, Deano, you’re truly in the right place.”  
  
Before the hunter can speak again, the space around him blurs, the air thick with what feels almost like static electricity as his surroundings change and he’s thrown into his fantasy world.

§

Dean’s flicking through the channels on the shitty motel TV when Sam comes out of the bathroom after his shower. The older Winchester has to force himself not to turn and look, because just lately Sammy has taken to getting changed in the main room rather than the bathroom, claiming he doesn’t like putting clothes onto clammy skin in the humid air. The kid has a point, but right now that’s not what concerns him.  
  
A year ago his brother didn’t show any more skin than necessary, always demanding privacy and locking himself in the bathroom to dress and undress, but since he hit a growth spurt a few months ago things have changed. He’s doing more workouts outside of their usual sparring sessions and whatever sport he’s involved in at school, he’s doing more sit ups in their motel rooms and generally seems a lot more confident in his body. Dean would be proud of him - he’s a Winchester after all and they’re a good looking family - but this is different. Sam’s back and arm muscles are more defined, his shoulders broader and he has abs that most other kids would kill for. He’s long, lean and gorgeous, and _that’s_ the problem. Dean can’t keep his eyes off his newly fifteen year old brother, and not in the ‘I’m proud of you, kid’ way he should be, it’s more the ‘I want to fuck your brains out, kid’, way, and it makes the older teen feel sick with shame.  
  
It’s not long before Dean’s eyes inevitably wander over to his brother and he’s just in time to see Sam stepping into a pair of boxers. Thankfully he manages to keep his eyes on Sam’s abs instead of letting them stray further down, but even that, _the sight of all that beautiful skin_ makes his mouth water. He quickly skims his eyes over his brother’s chest, gaze automatically being drawn lower with the movement of Sam pulling on a pair of sweats, the waistband snug under his junk, framed for just a few seconds, the outline of Sam’s soft yet ample cock clearly visible though the light grey cotton.  
  
“See something you like?” the teen asks in a mocking tone, making Dean choke on his own spit.  
  
“What? No, God, _shut up_ , Sammy,” he shoots back, plastering the most disgusted look he can onto his face, hoping it hides his guilt.  
  
“Dude, it was a joke,” Sam laughs, “no need to freak out.”  
  
The older teen’s eyes flick between Sam’s face, chest and abs and he feels his cock twitch in his jeans, “I’m not freaking out, why would I freak out?” he’s aware he sounds defensive so he clears his throat and keeps his tone as casual as possible, “Quit being such a bitch, Sammy.”  
  
“It’s _Sam_ , and what’s the matter with you, jerk?” his brother asks, confusion clear in his voice.  
  
Dean looks at his brother, then - at his face, finally - his mind racing with something to say, “Fuck you!” is the best he can come up with. He grabs his own change of clothes and heads for a shower, careful to ignore the ache in his cock at the smell of Sam’s shampoo and the thought of him standing in the same spot, wet and naked only a few minutes ago. He groans, washing himself quickly once he climbs under the spray, thinking about the putrid intestines of the dead racoon they almost hit with the car earlier, which soon makes the problem go away.  
  
In actuality Dean got dressed, avoiding looking at his brother’s still half naked form sprawled out on the bed, told Sam not to wait up and banged the first willing chick at the bar closest to the motel; but here’s where it changes into Dean’s fantasy version. Instead of just accepting that his brother was going out, Sam argued, saying he wanted them to spend some time together, watch a movie, maybe steal a couple of dad’s beers, and of course Dean gave in the minute his baby brother turned on the puppy eyes.  
  
Soon they were side by side on Sam’s bed, Dean in boxers and t-shirt and Sam still shirtless. One minute they’re drinking beer, laughing at some cheesy Abbott and Costello movie they’ve seen countless times, and the next, because this is a fantasy after all, Sam is running one of his long fingers slowly up Dean’s bare thigh. The older teen’s breath catches in his throat as the digit stops just shy of the hem of his boxers where they’re rucked up half into the crease of his leg. He swallows audibly before turning slowly to look at his brother.  
  
Sam’s cheeks are flushed, his eyes glassy, pupils wide and he’s breathing fast and shallow, “Dean?” he says, and there are so many things that could mean but as his baby brother’s eye flick from Dean’s mouth to his eyes, it’s pretty clear what he’s asking. The older teen’s skin tingles where Sam traces back down towards his knee then lightly digs his nails into the skin as he moves back up, his fingertips pulling Dean’s underwear up a fraction more.  
  
“Sammy,” Dean croaks, “we can’t.”  
  
“Can’t we?” the younger boy replies with a raised eyebrow.  
  
Dean covers Sam’s hand with his own but doesn’t push it away, can’t bring himself to, “We’re brothers,” he says, stating the obvious, “people…”  
  
“Fuck people,” Sam replies, cutting his brother off, “don’t you want to? Don’t you want _me_?”  
  
“Jesus, Sammy,” Dean huffs, lifting his hand to cup his brother’s jaw, inadvertently giving the kid free reign with his own, “you gotta know I do, baby boy, wanted you for so long.” He knows he’s sounds like a giant pervert, but it’s his fantasy, he can say whatever the fuck he wants.  
  
Sam flashes him a dimpled smile then licks his lips and closes the distance between them. The kiss is soft but not hesitant, it’s confident in a way Dean hadn’t expected. Sam’s lips are soft, smooth and sweet, and when he slides his hand up those last few inches and rubs over Dean’s dick he takes advantage of his brother’s gasp and sweeps his tongue into the older teen’s mouth. They kiss until they have to gulp down air, by which point they’re both hard, Dean can feel not so little Sammy pressing into his hip.  
  
In the blink of an eye Sam is naked on his back, too long but perfect hair fanned out over the pillow and looking up at his brother like he’s the most delicious thing he’s ever seen. Dean knows that feeling well. When he leans down to take that sinful, candy pink mouth in another kiss he realises that he’s naked, too, his hot skin meeting Sam’s and firing up his blood even more. They both moan into the kiss when the older teen brushes his fingers over his brother’s ribs and nipples, “So fucking beautiful,” he whispers when he pulls back, smiling to himself when Sam’s cheeks pink underneath the already flushed skin.  
  
Dean kisses his way down his brother’s neck and chest, pausing to lick, suck and bite his nipples just to feel the kid squirm, moan and leak fat drops of pre-come onto his taut stomach. He dips his tongue into Sam’s belly button, grazes his teeth over the edges, does the same to both hips before breathing in the musky, salty sweet scent of Sam’s cock. When he licks at it, Sam gasps and Dean moans at finally getting to taste his brother, quickly wrapping his lips around the head to lick and suck the kid into a frenzy. He works two fingers deep inside his brother’s tight ass after opening him up with his tongue, pumping steadily in and out as his other hand strips Sam’s cock until he comes like a fountain all over himself, the bed and Dean’s hand. It’s too much for Dean to take, grabbing Sam’s hand and wrapping around his cock, pumping a few times before he shoots over his brother, their come mingling over Sam’s skin.  
  
The air shimmers slightly and Dean finds himself sitting on the edge of the bed with a wet warmth around his cock. His head is swimming and when he finally manages to open his eyes it’s to see Sam on his knees, a blissed out look on his face as Dean’s cock slides in and out of his swollen mouth at a steady pace, making the older teen moan at how good it looks and feels. A few thrusts of his hips and he’s crying out and tugging on Sam’s silky hair as he does, vaguely registering the feeling of Sam’s own come hitting Dean’s shin even as he’s coming hard down his little brother’s throat.  
  
A blink later has the older Winchester kneeling between his brother’s spread legs, the kid’s pink, wet mouth hanging open in pleasure as Dean’s cock slowly pushes into his slick hole. Dean can’t decide which is hotter, Sam’s face or the way his cock is opening and stretching that tiny opening and being swallowed up by it. It’s like he’s lost the ability to speak, but that’s fine because it means he can listen to Sam’s moans, the steady stream of his own name and the begging that falls from his baby brother’s lips as Dean fucks him slow and steady, tightly lacing their fingers until Sam comes, his ass spasming around his brother’s cock until Dean empties his slick load into it.  
  
Another blur and it’s Dean that’s flat on his back. Sam’s straddling him, working his hips to rock slowly back and forth to ride Dean’s cock buried deep inside him. If Sam’s desperate and filthy kisses weren’t already stealing Dean’s breath, the sight of his baby brother’s beautiful teenage body writhing above him, flushed skin beaded with sweat, eyes glazed with lust and the most exquisite sounds coming from his pretty pink mouth, would. As soon as Sam pulls back from a wet, messy kiss that’s more tongue than lips, large hands are on his slim hips, guiding him up and down. Always the quick learner the kid starts to bounce on Dean’s cock, bliss for both of them, the smack of sweaty skin as loud as their moans and grunts as they work up to what’s got to be their fifth or six orgasms of the night, it’s been so much pleasure Dean can’t tell.  
  
Sam collapses onto his brother’s chest, utterly exhausted. He barely reacts when Dean rolls them and his cock slips out of the younger boy’s come soaked hole, or when the older teen sweeps his fingers through the mess and pushes it back inside where it belongs. He needn’t bother, he’s already filled Sam up several times over, it’s so deep inside he’s going to be dripping for days at this rate. A shiver of delight runs down Dean’s spine at thought, knowing he’s marked Sam as his in the only way he hadn’t been able to up until now.  
  
He presses soft kisses to Sam’s forehead, nosing at his sweat soaked hairline just to pull in the scent of him, warm and close, exactly where he should be. Dean needs to rest, he’s exhausted, too, so he lies down, pulling his brother’s slim frame across his chest and holding him tight as he drifts off to sleep with memories of all the things they’ve done to each other.

§

Dean feels his stomach lurch and there’s a sharp pressure like someone’s reaching behind his belly button and hauling him into another world. Around him now is the stench of sulphur, death, blood, stale sweat and fear. His eyes are still closed and he doesn’t need to open them to know Alistair is only inches away from him. He can hear his ragged breath, the soft moan falling from his lips telling him the bastard’s hard, it always happens when he’s really put Dean through it, when he’s dripping in blood and sweat, begging for the torture to stop, the sick fuck... though right now Dean doubts he has any right to think that of anyone else considering what he’s just been doing.  
  
“That was quite a show you two put on, Deano, I’m impressed,” the demon practically purrs. A cold, sharp blade traces down the hunter’s face making him flinch, but it doesn’t sink into his flesh like he expected. Instead it traces his lips, nose and under his eyes, then Dean really tenses, “Look at me,” Alistair says, cupping his chin in spindly fingers. Not feeling like there’s a choice, green eyes meet inky black, “I like you, Dean, we both know that, so I’m going to show you a kindness.”  
  
“Fuck you, you don’t know the meaning of the word!” Dean spits out before he can stop the words. _Shit_!  
  
A low chuckle fills his ears and to his surprise the demon’s eyes are back to their normal blue and has a genuine smile on his face, “Oh, but I do, darling, and to prove it I’m going to give you _two_ days off the rack.”

§

Dean’s been back in the cycle of being broken and made whole again for a week, doing his best to bring all the details of his time with fantasy Sam clearly into his mind the whole time as his flesh is burned, cut and torn. He’s been desperately clinging onto the happiness he felt at finally getting to be with his brother in the way he’s wanted to for years, and he manages it for the most part...right up until fresh self loathing runs through him one time too many. It doesn’t matter that none of it actually happened, the guilt itself is very, very real.  
  
The next time Alistair makes his offer to take him off the rack if he puts souls on he accepts without hesitation, and when he makes his first cut into unmarked skin there are tears rolling down his face, “I’m sorry, Sammy,” he croaks, “I’m so sorry.”


End file.
